SYNTHESIS OF THIAMONO- AND THIABICYCLANES FROM SODIUM SULFIDE AND METHANETHIOLATE

Authors

  • Л. А. Баева Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, Ufa 450075
  • А. Д. Улендеева Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, Ufa 450075
  • О. В. Шитикова Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, Ufa 450075
  • Н. К. Ляпина Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, Ufa 450075

DOI:

https://doi.org/10.1007/6555

Keywords:

1-[5-acetyl-3-(methylthiomethyl)tetrahydro-3-thiopyranyl]-1-ethanone, 4-methyl-1-methylthiomethyl-7-thiabicyclo[3.3.1]non-3-en-2-one, sodium methanethiolate, sodium sulfide, condensation

Abstract

1-[5-Acetyl-3-(methylthiomethyl)tetrahydro-3-thiopyranyl]-1-ethanone was obtained by the interaction of sodium sulfide and sodium methanethiolate with formaldehyde and acetone. The intramolecular crotonate condensation of the product leads to 4-methyl-1-methylthiomethyl-7-thiabicyclo[3.3.1]non-3-en-2-one. The participation of 3-methylthiomethyl-3-buten-2-one in the formation of a thiamonocyclane is clarified. A probable scheme for the conversions is proposed.

How to Cite
Baeva, L. A.; Ulendeeva, A. D.; Shitikova, O. V.; Lyapina, N. K.  Chem. Heterocycl. Compd. 2009, 45, 11197. [Khim. Geterotsikl. Soedin. 2009, 1494.]

For this article in the English edition see DOI 10.1007/s10593-010-0407-3

 

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Published

2022-02-09

Issue

No. 10 (2009)

Section

Original Papers